Feels like you are trading risk for unforeseen problems and delays in the engine work for risk of an engine failure on a long trip.
Not a simple question as you know!
I can tell you my 4bbl, cam, and lifter swap snowballed beyond reason (I don't even want to talk about it), but that's me and not you.
You do such nice work I don't see you settling for just swapping lifters. Mission creep beyond what you hope for can happen, so planning for the worst might help you prepare.
Maybe compare "what's the worst that can happen" for the two scenarios?
I personally have never done a leak-down test, but that might help you understand the source of the low compression pressure?
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